


Monopoly Fun

by TakatoTheDreamer



Category: Digimon - All Media Types, Digimon Adventure, Digimon Adventure Zero Two | Digimon Adventure 02, Digimon Adventure tri.
Genre: ....I guess? I'm bad at tagging, Kinda, M/M, Male Vibrator, Masterbation, Monopoly meets Truth Or Dare, Oral Sex, Sex Toys, new relationships
Language: English
Status: Completed
Published: 2020-06-19
Updated: 2020-06-19
Packaged: 2021-03-03 20:20:53
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,096
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24811471
Author URL: https://archiveofourown.org/users/TakatoTheDreamer/pseuds/TakatoTheDreamer
Summary: Tai and Izzy have just started going out. They were already best friends, but there are things even best friends don't talk about. Izzy has a fun way to do just that.
Relationships: Izumi Koushirou | Izzy Izumi/Yagami Taichi | Tai Kamiya
Kudos: 12





	Monopoly Fun

**Author's Note:**

> As always this is a trade. In the doc file I had actually googled and got screenshot images of the cards and pasted them in, but I'm pretty sure I can't post them here, since they aren't mine. I do know it's a little boring to say 'The card said: .....' but there's nothing else I can do for that ^^. Enjoy!

Tai knocked on Izzy’s apartment door. He had been dating him for a few days now. It was a weird feeling. They had secretly been in love with each other for years and they had finally confessed. While they were both happy, it was a little awkward going from best friends to boyfriends and there was still so much about each other they didn’t know. Things best friends wouldn’t share, but boyfriends would.

Finally, Izzy opened the door with a smile.

“Hey Ta-”

Izzy was cut off by Tai’s lips on his. After the surprise wore off, Izzy returned the kiss passionately, putting his arms around Tai’s torso and pulling him inside.

Izzy blushed as he broke the kiss.

“I wasn’t expecting that,” Izzy said, smiling as he straightened up his orange button down shirt.

“Well I wasn’t expecting you to be so cute when I opened the door.”

Izzy blushed harder as he walked over and opened his fridge.

“Do you want something to drink?” Izzy asked politely.

“Nah I’m okay for now. That restaurant we want to go to doesn’t open until 5 and it’s only 2, so we have a long time. What do you want to do in the mean time?”

“Well…” Izzy said, pulling out a bottle of oolong tea. “I had a fun idea. Monopoly.”

Tai raised his eyebrow in surprise.

“I mean...” Tai replied, slowly, “I don’t hate Monopoly but… is that really what you want us to do on our first full day together?”

“I created my own rules though. It’s mainly played like the regular game but when it comes to paying taxes or rent… well, you’ll see. It will be good for us, I promise.”

Tai nodded. “Okay, let’s do it!”

With that, Tai followed Izzy in the living room, surprised to see the game already set up on a card table in the middle of the room with two metal chairs.

“What piece do you want to be?” Izzy asked, sitting down.

“The thimble.”

Izzy blinked. “Guess you haven’t played Monopoly for a while. That’s not a playable piece anymore.”

“What?” Tai crossed his arms. “That’s no fun. I guess I’ll be the top hat then.”

“Okay,” Izzy said, putting the top hat on Go. “And I’ll be the cat.”

“There’s a cat in Monopoly??” Tai asked, surprised.

Izzy slunk back in his chair awkwardly. “It’s… what replaced the thimble.”

“...Oh.”

“I can use a different piece...”

“No no!” Tai said, holding his hands up. “You can use the cat.”

“Okay,” Izzy said, putting the piece down.

“First we roll to see who goes first.” Izzy said as he tossed his dice, revealing a 9. Tai then rolled and got a 6.

“I go first,” Izzy said, handing Tai 1500 Monopoly Dollars.

Izzy then rolled double 3’s, a 6, which landed him on the first light blue property.

As he moved, Izzy spoke. “Rolling doubles means you go twice.”

Tai chuckled. “Is this one of your special rules?”

Izzy shook his head. “No. It’s standard. You roll doubles, you go again. Roll doubles again and you can go again. But if you roll doubles a third time, you go straight to Jail.”

Tai smirked. “Do I get a conjugal visit?”

Izzy rolled his eyes with a smile. “The fee for getting out of Jail is only $50, so no.”

“You know that could be the funnest part of the game...”

“We’ll have fun, don’t you worry,” Izzy said, buying the first light blue property. He then shook the dice and dropped them again and rolled a 3, landing on the third light blue which he bought.

“Your turn, Tai.”

Tai took the dice and rolled an 11. Tai then bought the first light pink.

It was Izzy’s turn again and he rolled an 8, which landed him on Community Chest. He looked at Tai.

“This might be where my special rules come in,” he said as he flipped the card over in a way Yugi Mutou would announce to the opponent he had activated his trap card.

The card said: ‘Doctors fee, pay $50.’

  
  


“Here are my rules,” Izzy said as his lip twisted in excitement. “For taxes, fees, and rent under $100, we have a choice. We can pay or we can give the other the chance to ask anything they want and the one paying has to answer honestly, no backing out.”

“What about over $100?”

Izzy’s face turned the slightest bit red, so slightly that Tai didn’t notice.

“We’ll get there.”

Tai tilted his head, wondering what Izzy had in mind. “So, am I asking a question?”

Izzy stuck out his tongue. “Well that was an easy question. Guess my rent is paid...”

“Nooo!!!” Tai said, waving his arms in the air. “That wasn’t my question! That’s not fair!”

“I’m kidding, Tai.” Izzy said, with a smile. “Ask me anything.”

“When did you first start having feelings for me?”

Izzy looked away, awkwardly. He wasn’t expecting this question.

“A long time,” Izzy said, embarrassed.

“How long?”

Izzy looked back at Tai.

“I’m honestly not sure. You were the first person my age to not treat me like a loser. Yeah, we went to the digital world soon after and everyone else was nice to me, but I still got that vibe from a few of them for a while. But you trusted me. When the group said they trusted you to make a choice, you said ‘Okay, then Izzy chooses.’ You were the greatest friend I ever had. After a while it just slowly grew into more. I really can’t tell you when that started.”

Tai nodded. “When did you know for sure, though?”

Izzy took a drink of his tea before replying.

“We were in high school and it was close to Valentine’s Day. You asked me if I liked anyone. I started to think about it and it just clicked.” Izzy had a sudden thought. “Were you trying to see if I’d say you?”

Tai opened his mouth to speak, but instead, he smirked. “Actually, you have to earn that question!” And with that, he took the dice and threw the dice across the board, snake eyes, landing him on the second pink, which he bought, and then he went again.

This time, he rolled a 9 and landed on Chance.

The card said: ‘Advance to Bordwalk.’

“YES!” Tai exclaimed as he purchased the last and most expensive property on the board, the second dark blue.

Izzy noted to himself to try and keep the other blue away from him as he took his turn. He rolled a 9, landing him on the first yellow which he bought.

It was Tai’s turn and he rolled a 7, landing him on the first light blue which Izzy already owned.

“Aww man...” Tai grimaced. “Now I guess I have to let you ask a question for 6 whole dollars...”

Izzy held a finger up as he explained. “That’s up to you though. You can just pay the $6. That’s the way I set it up.”

Tai thought about it for a moment. It would be easy to just pay it, but he knew that the fun of this game was to ask questions.

“I choose to let you ask a question.”

Izzy thought about it. There were several questions he wanted to ask. Who knew how many chances he’d get before they got into bigger amounts owed? Finally he settled on a question.

“How many guys have you been with before me?”

Tai shifted awkwardly as he looked back down at his money.

“So $6…?”

Part of Izzy wanted to let Tai pay the $6 and let it go as the reaction Tai gave made it seem like it was a big number, but Izzy decided he would be thinking about it too much himself. Now he HAD to know.

“Nope, once you’ve committed to a question, you can’t switch.”

Tai looked back at Izzy, looking a little scared before looking back down at the board embarrassed.

“...No one.”

Izzy was taken aback. “N-no one? But how is that possible? You’re… well, you’re you!”

Tai smiled a little, slowly looking back up at his boyfriend.

“I just never found the right person. I wanted my first time to be great and I just never dated any great guys. But it worked out because you will be my first.”

Izzy blushed at the comment as he debated about joking that he’d been with the entire computer club in college, but decided against it as he took his turn. He got a 4 and went to jail.

“Gah!” Izzy yelped as he moved his piece to jail.

“Guess that means I get to ask a question now,” Tai said with a smirk.

“Not this turn,” Izzy said, handing Tai the dice.

Tai rolled a 7. He landed on the last pink he needed, completing the set!

“Awesome! And you’re in jail right in front of my properties so I’m going to build houses!”

Izzy watched as Tai spent all but $60 building 8 houses. Three on two, and two on the first one. He wanted to speak up about that not being very smart this early in the game, but it was playing into his plan. And it wasn’t like he COULDN’T land there next turn.

After Tai was done building, Izzy spoke.

“Well, I could roll doubles to try and get out of jail that way, but I choose to let you ask a question.”

“Okay,” Tai said, looking over at Izzy’s Pineapple sitting on the couch.

“How much porn do you have on your laptop?”

Izzy blushed as he looked at it. “I-I don’t have any porn … … … on my laptop….”

“Oh?” Tai said, raising an eye brow. “So you DO have porn somewhere?”

Izzy debated with himself. Part of him wanted to say that Tai asked his question and he answered it so that was all he got. But, he knew it was going to come up again and he wanted other questions to be asked so he decided to explain.

“I have a desktop in my bedroom. That’s where my porn is. No one ever is in my room so there’s no chance of anyone finding it. Whereas, I take my Pineapple everywhere, so I have a policy of not ever looking up porn on it. If I get distracted and walk away, I don’t have to worry about anyone snooping – I’d like to think none of my friends would anyway, but even so.”

Tai nodded. “So… how much?”

Izzy looked down awkwardly. “I… I don’t… really… look at ‘real’ porn…. I have a collection of… drawings...”

Tai blinked. “Yaoi?”

Izzy’s head shot up. “You know about Yaoi?!”

Tai rubbed his hands together as a smile formed on his face. “We need to share collections then.”

Izzy then took the dice and rolled.

“COME ON 4!” Tai said, hoping Izzy would land on his hotel but instead he rolled a 6, landing him on the first orange which he bought.

Tai then rolled a 9, taking him to Chance:

The card said: ‘You have been elected chairman of the board. Pay each player $50.’

Tai looked at his money. “I don’t have much of a choice. What’s your question?”

“Earlier, when we were talking about high school Valentine’s Day… Did you ask me to see if I would say you, so we could be together?”

Tai smiled. “Not exactly. I was… I don’t know how to describe it… I was somewhat aware of the possibility I had feelings for you, but I hadn’t really put my finger on it yet. I guess I asked to see what you would say, to gauge my own reaction. And when you said you didn’t like anyone, it gave me hope. I guess you just said no to not have to explain it?”

Izzy took a drink of his tea before responding. “I did say it just clicked earlier, but it was more that later in the day I thought about your question and that’s when it clicked.”

“I see,” Tai said, handing Izzy the dice. Izzy rolled a double five, which took him to the first yellow he already had. He then rolled another double five, landing him on chance.

The card said: ‘Advance to GO! Collect $200.’

Izzy frowned. It sucked a little getting that when he was so close to Go anyway, but he knew that’s just how the game went sometimes.

Once he got to Go and collected $200, he rolled again, hoping to not get doubles.

This time he rolled an 8 but not doubles, landing him on the second light blue which he needed to complete his set!

Izzy was a bit more conservative with his houses but since they were only $50 compared to Tai’s houses being $100, he built 2 houses on each and gave the dice to Tai.

Tai rolled a 12, a double six, taking him to the last green. Tai groaned.

Izzy looked up with a twisted smile. “I take it we can forgo an auction and I can just buy it for $61?”

Tai nodded, annoyed, as he went again. This time he rolled a 10, which took him past Go, but landed him on $200 Income Tax.

“Gah!! Might as well not even collect the Go money then...”

“Well you can and you do need the money…” Izzy said. “We haven’t gotten to my rules for when the fees are over $100. But if you want the Go money you have to agree to the rules before I tell you what they are.”

Tai was unsure about this slightly devious side of Izzy, but he decided to just go with it.

“Alright, I agree,” Tai said, taking the Go money. “So what are these rules?”

Izzy smirked. “For taxes, fees, or rent over $100, you have to do whatever I want for a certain amount of time: 1 minute per $100. Lets say the rent was $150 – or anywhere in between. It would be your option to say just one minute, and pay the $50 or go for two minutes and earn $50 back. If it’s more like $120 or $180, that might have a bigger influence on the choice. But since this time was $200, it’s just two minutes flat.”

“Okay. What do you want me to do for two minutes?”

As Izzy began to answer, he reached down to his zipper. “I have a fun way for you to pay your debt.”

With that, Izzy’s erection through his boxers popped out. Tai couldn’t help but lick his lips. On one hand, he wanted their first time doing anything to be special, but, he would be lying if he said the surprise to him and spontaneity from Izzy wasn’t super hot.

“I don’t have any experience though. I don’t think I could get you off in two minutes.”

“Oh no,” Izzy said, shaking his head. “That’s not the goal here. I don’t want you to get me off or even suck my dick.” He undid his belt, pulling down his khakis and his boxers to his knees. “I just want you to lick my dick for two minutes.”

Tai tried not to drool as he stared at his boyfriend’s package for the first time. His dick was average length and a good shape. A bit thick and a little wide. His balls were plump and his pubic hair had been trimmed.

Izzy on the other hand had considered telling Tai to suck his dick, but he wasn’t sure he’d have the willpower to make him stop. He thought that by just licking he wouldn’t be quite that far gone.

Tai then got on his knees and crawled over to Izzy. He stuck out his tongue and-

“Wait!”

Izzy said, causing Tai to look up. Izzy was opening the stopwatch app on his phone and set it for two minutes.

“You can start… … … … NOW!”

Tai began to lick the very top before exploring around the head.

“Mmmm...” Izzy groaned as he wasn’t expecting just his tongue to feel so great. This was their first sexual contact and Izzy didn’t think it would affect him so much, but having Tai’s lips that close to his dick, feeling his breath on his shaft… it was just too much.

Tai continued to slowly lick around the head, up and down, back and forth, before moving on to the base.

Izzy looked at the stopwatch. It had only been 50 seconds. If this went on too much longer, he really might not be able to stop.

As Tai continued to explore his boyfriend’s dick, he took in everything about it. The taste, the texture, the smell… he wanted to enjoy every bit of it. He had been waiting for this for a long time.

Izzy stared at the stopwatch. These seconds were passing like minutes. He didn’t know if he could hold it together much longer.

Tai continued to lick around the thick base, exploring every inch of his length before slowly making his way back to the tip. He slowly drug his tongue around as -

“TIME’S UP!” Izzy exclaimed, panting.

Tai was surprised time went by so fast. He chuckled to himself, ‘I guess time flies when you’re having fun!’ he thought. He was unable to see Izzy turning off the alarm, with another 30 seconds left.

“My tongue was too much for you to handle, hmmm?” Tai said with a grin as he got back up, causing Izzy to blush as he pulled up his pants.

“...It was hard to tell you to stop...” Izzy replied, as he took his turn and got a 4, landing him on the electric company, which he bought.

Tai took the dice and rolled a 6, landing him in jail, just visiting. Since there was a chance Izzy would land on his last house, he built two more: one on the cheapest pink to make the houses even and then on one the most expensive and last, hoping Izzy would roll a two. Izzy knew that wasn’t a smart idea as it only left Tai with $60, but after what he had started with Tai, he needed the game to be over.

Izzy then rolled a 4, landing him on the first orange which he already had.

Tai then took the dice and rolled a 12, taking him to chance. Izzy crossed his fingers it was something that would take him out.

As Tai flipped the card over, he grimaced.

The card said: You are assessed for Street Repairs. Pay $40 per HOUSE and $115 per HOTEL.’

Tai facepalmed. “If I have to pay $40 per house, guess I’m out.”

“So you are officially declaring bankruptcy?”

“Yeah, I am,” Tai said, looking at the clock. “We still have a while before the restaurant opens. Wanna play again? That was fun!”

“We aren’t done yet,” Izzy said, calmly.

Tai blinked. “What do you mean?”

“With my rules, whoever goes bankrupt has to do whatever the other one wants.”

Tai looked down at Izzy’s crotch. “Does that mean I get to finish the job I started?”

Izzy shook his head. “No, I’m going to introduce you to one of my… special toys.”

Tai gulped. What exactly did that mean?

“Follow me into the bedroom, Tai,” Izzy said, as he stood up and walked into his room.

Tai had never been in it before. It was small but not tiny and it had a computer desk in front of his bed. Now he knew why.

“Take all your clothes off, Tai,” Izzy said, as he started to get undressed himself.

Tai did what he was told, laying his clothes over Izzy’s computer chair.

Izzy also took a moment to see Tai’s crotch for the first time. Tai couldn’t help but notice.

“Like what you see?”

It was true, Izzy did. Part of him wanted to cancel the plan and just have Tai’s dick in his mouth like he always wanted. But he had planned this. He wasn’t backing out now.

“I do. Lie down on the bed.”

Tai did as he was told as Izzy walked over to his dresser drawer. Izzy pulled out a box and a bottle of lube.

As Izzy got closer with the box Tai could read what it said: ‘Automilker’.

Tai’s dick twitched, getting slightly hard as he was wondering just what he was in for.

Izzy opened the box and pulled out a cylindrical device with a hole in the bottom and a flap on the top.

“This is a milking machine,” Izzy said, showing it to Tai. “Or at least that’s what they call it. I’ve seen some other interesting ones in drawings, but basically it’s a male vibrator.”

“I never knew they made such a thing!”

“I just found out recently,” Izzy said, as he pressed a lower button, turning the main part on. “It says to use lube but to start with we won’t.”

With that, Izzy sat on the bed and slid the machine over Tai’s semi-hard on. Instantly the pulses through the machine caused Tai to become fully erect so that his dick head was almost sticking out the other end. The vibrations and pulses affecting different areas of his cock. He could see why Izzy liked this and wanted to share it with him.

“Now, the machine does say it’s supposed to be hands free,” Izzy explained, “But I don’t find that to be entirely true. It’s more fun to use hands as well.”

With that, Izzy began to gently squeeze the back of the machine, causing the front of Tai’s dick to be pressed against the vibrations even more and the back of his dick to feel more as well. Tai whined as the vibrations were pretty intense and he could feel something building inside of him.

“Okay, it’s time to add lube,” Izzy said, as he grabbed the bottle and pulled Tai’s dick out of the machine for just a moment. He then took a handful of lube and spread it all over Tai’s cock, mainly for lube but he lingered in a few areas to tease Tai.

Tai whimpered, but the truth was, after the vibrations, Izzy’s hand felt kind of lame. He hoped it was just because his dick was still vibrating.

Meanwhile, Izzy was tempted to just keep stroking Tai and get him off with his hand. He wanted to feel his dick twitch in pleasure, he wanted to feel and see him cum. But he wasn’t backing down from his plan. After he was satisfied, he put the machine back on Tai.

Tai was instantly overcome with pleasure. Not only with the vibrations coming back but the lube was moving with the vibrations, creating an entirely new feeling.

Tai groaned loudly as Izzy began to squeeze it from the back as he did before, making the vibrations tighter and the lube feel even better. Then he began to move it up and down slightly.

Tai’s toes were curling he was in so much pleasure!

Izzy then took a moment to get some more lube which he spread over the flap on the top. Tai wasn’t sure what was going on. But then it became clear: Izzy pulled the flap over Tai’s tip and hooked it into the back before pressing another button, turning the flap on! His entire dick was now vibrating.

“AHHH!!!!” Tai moaned loudly as the pulses shot through every inch of his dick and the vibration of the lube, which caused a wave of sensations from the lube dancing.

“Iz-zy… I’m gonna...”

With that, Izzy pulled the machine tighter again at the back and started stroking slightly. Tai twitched and groaned as he had the most intense orgasm of his life.

The only bad thing was because of the flap, Izzy couldn’t see when Tai had finished.

“O-okay-I’m-d-done...” Tai stuttered, still jittery.

With that, Izzy took the machine off, turned it off, and set it to the side, before lying next to his boyfriend, and giving him a kiss.

“Exactly what part of that was punishment?” Tai asked with a smile.

Izzy blushed a little. “I thought you would judge me for my toy. But I’m glad you didn’t.”

Tai kissed him back. “I’m gonna lose from now on.”

With that, they cuddled.

The En-

“WAIT!” Tai suddenly spoke up. Izzy looked over curiously.

“If you would have lost, would I have known about the punishment rule??”

“...Nope.”

The End

  
  


  
  



End file.
